Abstract
The mild and efficient generation of benzenesulfenic acid by the thermolysis of Et 2-ethoxycarbonyl-3-(phenylsulfinyl)butanoate in refluxing dichloromethane, its in situ trapping with (E)- and (Z)-1-methoxy-2-buten-3-yne to form (E)-1-methoxy-3-(phenylsulfinyl)-1,3-butadiene and (Z)-1-methoxy-3-(phenylsulfinyl)-1,3-butadienes resp. proceeds in high yield. The lithium perchlorate catalyzed Diels-Alder reaction of (E)-1-methoxy-3-(phenylsulfinyl)-1,3-butadiene with both sym. and unsym. carbonyl activated dienophiles proceeds with complete regioselectivity and in some cases complete endo-selectivity.
| Original language | Undefined/Unknown |
|---|---|
| Pages (from-to) | 3967-3974 |
| Number of pages | 8 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Issue number | 23 |
| Publication status | Published - 1998 |
Keywords
- Diels-Alder reactions
- 3-butadienes
- benzenesulfenic acid
- regioselectivity
Cite this
Adams, H., Anderson, J. C., Bell, R., Neville Jones, D., Peel, M. R., & Tomkinson, N. C. O. (1998). The synthesis and Diels-Alder reactions of (E)- and (Z)-1-methoxy-3-(phenylsulfinyl)-1,3-butadienes. Journal of the Chemical Society, Perkin Transactions 1, (23), 3967-3974.